5-(N-benzyl-N-benzoxycarbonylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enono-1,4-lactone | 140193-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(N-benzyl-N-benzoxycarbonylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enono-1,4-lactone
• CAS: 140193-68-6
• 化学式: C₂₅H₂₇NO₆
• 分子量: 437.492
• InChiKey: SXHYIVRBRBEPJP-ZOAFEQKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-(N-benzyl-N-benzoxycarbonylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enono-1,4-lactone 在 二环己烷并-18-冠醚-6 、 palladium dihydroxide potassium permanganate 、 dimethyl sulfide borane 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 2,3;6,7-di-O-isopropylidene-1,5-dideoxy-1,5-imino-D-glycero-D-allo-heptitol
  参考文献：
  名称：

  Total synthesis of 1,5-dideoxy-1,5-iminoalditols

  摘要：

  Enantiomerically pure 1,5-dideoxy-1,5-imino-D-glycero-D-allo-hepitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-D-glyceraldehyde-N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4, followed by diastereoselective anti,cis-dihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9.

  DOI：

  10.1016/s0040-4020(01)88132-1
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 三氟化硼乙醚 、 碳酸氢钠 、 magnesium sulfate 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 5-(N-benzyl-N-benzoxycarbonylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enono-1,4-lactone
  参考文献：
  名称：

  Total synthesis of 1,5-dideoxy-1,5-iminoalditols

  摘要：

  Enantiomerically pure 1,5-dideoxy-1,5-imino-D-glycero-D-allo-hepitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-D-glyceraldehyde-N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4, followed by diastereoselective anti,cis-dihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9.

  DOI：

  10.1016/s0040-4020(01)88132-1